Chiefs might have made a mistake letting Orlando Brown Jr. walk after all

"Hindsight is 20/20." This phrase is always applicable when it comes to looking back on key decisions in the draft of free agency. It's also worth noting that the Chiefs' success and Super Bowl rings are certainly well-earned but don't exist in a vacuum. For instance, the Chiefs drafting Skyy Moore was not the only way for them to become back-to-back champions. Certainly, if they could redo that selection they would. So looking at the Chiefs tackle situation today and saying "Well, they won a Super Bowl" makes for shallow analysis.

As it sits today, D.J. Humphries, a 30-year-old tackle signed in December coming off a torn ACL, might be the most important factor for the Chiefs' ability to win three straight Super Bowls. The Chiefs' tackle play has been crippling in several games despite paying $20 million a year for Jawaan Taylor and investing two Day 2 draft selections into the position.

Even more concerning is the answer to the Chiefs' left tackle problem still might not be on the roster. We'd all like to believe a redshirt year for Kingsley Suamataia might see him develop into a starting left tackle but the last plays we've seen from him are in line with bottom-tier tackle play. And Wanya Morris effectively made the Chiefs' offense incapable of functioning on black Friday because of his play.

The Chiefs have a tackle problem that isn't going away, so why did they let the best left tackle they've had since Eric Fisher walk?

The first and most obvious factor that went into the decision to let Orlando Brown walk was the cost. The Chiefs made a strong push to sign Brown after his first season in Kansas City. ESPN's Adam Schefter reported the Chiefs' final offer to Brown was a six-year, $139 million deal that included a $30.25 million signing bonus and $95 million in the first five years of the contract. A hefty contract that Brown turned down to play on the franchise tag in 2022. After that season, the Chiefs ultimately decided to not tag Brown a second time after they could not come to terms on a new contract.

After the first wave of free agency came and went without Brown having a new deal, he reached an agreement with the Bengals on a four-year, $64 million deal that included $31.10 million in guaranteed money. That's a noted step down from the contract the Chiefs offered him. The Chiefs let Brown test the market because he thought he was worth more than what they were offering him. He clearly misread that market and is now the 12th highest-paid left tackle.

Reality is, if the Chiefs could have Orlando Brown on the contract he is on now for the Bengals, that would've been a great deal for them—especially when you consider the fact that Brown is making just over $16 million a year while Jawaan Taylor is making $20 million a year to play right tackle. It's also worth mentioning that Brown has had a higher PFF grade than Jawaan Taylor, Donovan Smith, Wanya Morris, and Kingsley Suamataia over the last 2 years.

A lot of Chiefs fans had the perception that Orlando Brown Jr. was an awful player. Lots of this was centered around the way he would lose when he did lose. It also had to do with his body. At 6-8, 350 lbs., his body wasn't ever going to look the same as Eric Fisher. Brown had a habit of losing badly when he did lose, but he wasn't getting beat that often and brought a presence in the run game the Chiefs haven't had since he left. Brown was a suitable left tackle. He likely wasn't worth the contract the Chiefs offered him in 2022 but most contracts are overpays. The Chiefs effectively took that cash and gave it to Jawaan Taylor to be a lesser player at right tackle.

Another factor in letting Brown walk is the never-ending question of who is the left tackle on this team? The Chiefs have already invested two picks on the second day of the draft and plenty of free agency dollars into Donovan Smith and now D.J. Humphries. All for the team to still have no long-term answer at the postion.

As illustrated by my post above, the answer isn't to get ultra-aggressive at the top of the draft either. The Chiefs would've needed to get up to the top 15 of the draft to get a starting caliber LT. That would be a trade package similar to the Mahomes trade-up or more. Also, as our draft expert here at Arrowhead Addict, this class is drastically worse at tackle than the 2024 class. There is no Joe Alt or Olu Fashanu in this class.

Meanwhile, if Brown was here how much easier could it have been to draft and develop a right tackle versus a left tackle? Wanya Morris played right tackle almost exclusively at Oklahoma. Kingsley Suamataia played right tackle last year at BYU. Roger Rosengarten was taken one pick before Sumatatia and is the starting right tackle for the Ravens, and he currently grades dramatically better than Morris or Suamataia. Additionally, maybe the Chiefs are able to use one of those picks (Morris or Suamataia) on a starting corner who could be playing key snaps right now.

Again, all of this exists in the "hindsight is 20/20" analysis, but the best left tackle that has been traded and signed in free agency since Trent Williams was Orlando Brown. The Chiefs let that guy out of the building. The notion that the Chiefs can simply sign a left tackle of high quality in free agency is false. They don't hit the market. The same is true with trades. When teams get a quality left tackle they don't let him out the door.

We've already illustrated that as long as the Chiefs keep winning, it's borderline impossible for them to move up to the point in a draft class where they can secure a solid starting left tackle. So what avenue can this team take to find a long-term answer at left tackle?

Was Orlando Brown perfect? No. He had flaws. Was he better than any other option the Chiefs currently have? Yes. The Chiefs have won Super Bowls with and without Brown and are still in a place to do so again. However, the repeated questions about left tackle and the draft loom large for a Chiefs franchise set to answer questions at the same position this offseason.

When it comes to keeping Patrick Mahomes healthy and happy, that's not a question you want to leave unanswered. Now our hope is in D.J. Humphries returning after an ACL tear for a playoff run.